# US 9,040,554 B2 · Solid forms of nematocidal sulfonamides

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- Number: US 9,040,554 B2
- Document ID: US9040554B2
- Status: Granted
- Kind: B2
- Application number: 14/346,446
- Filed: 2012-10-05
- Published: 2014-08-14
- Granted: 2015-05-26
- Earliest claimed: 2011-10-13
- Assignees: E. I. Du Pont de Nemours and Company
- Applicants: E I Du Pont De Nemours and Company
- Inventors: Christian Hoffmann; William J Marshall; Rafael Shapiro; Richard A Berger
- Web page: https://patentgrep.com/patent/US9040554B2

## CPC

- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- A61P 33/00: Antiparasitic agents
- A61P 33/10: Anthelmintics
- C07D 471/04: Ortho-condensed systems
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Disclosed are solid forms of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide (Compound 1). Methods for the preparation of solid forms of Compound 1 and for the conversion of one solid form of Compound 1 into another are disclosed. Disclosed are nematocidal compositions comprising a nematocidally effective amount of a solid form of Compound 1 and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid carriers. Compositions comprising a mixture of a solid form of Compound 1 and at least one other nematicide, insecticide and/or fungicide are also disclosed. Also disclosed are methods for protecting a plant from nematodes comprising applying to the plant, or portion, or seed thereof, or to the growing medium of the plant, a nematocidally effective amount of Compound 1 comprising the polymorph Form A.

## Claims

### Claim 1

A polymorph of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide designated Form A characterized by a room-temperature powder Cu(Kα1) X-ray diffraction pattern having at least the 2θ reflection positions
2θ
30.367
29.131
27.995
27.611
26.49
25.973
25.604
24.285
23.582
19.789.

### Claim 2

A polymorph of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide as a 1 to 1 solvate with toluene designated Form TS characterized by a room-temperature powder Cu(Kα1) X-ray diffraction pattern having at least the 2θ reflection positions
2θ
28.913
26.942
25.672
24.451
23.316
22.429
20.325
19.053
18.603
12.871.

### Claim 3 (depends on 1)

A method for preparing the polymorph Form A of claim 1 comprising forming a slurry with a solvent of one or more solid forms of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide selected from the group of forms B, C, D, having a powder Cu(Kα1) X-ray diffraction pattern in accordance with that shown in FIG. 1, solvates, amorphous forms and mixtures of any of the foregoing with Form A and maintaining the slurry while the solid forms of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide convert to polymorph Form A.

### Claim 4 (depends on 3)

The method of claim 3 wherein the solid forms of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide comprises a mixture of polymorphs Form A and Form B.

### Claim 5 (depends on 3)

The method of claim 3 wherein the slurry is heated to a temperature between 30° C. and the boiling point of the solvent and agitated.

### Claim 6 (depends on 3)

The method of claim 3 wherein the slurry is agitated.

### Claim 7 (depends on 3)

The method of claim 3 wherein the solvent comprises water, a C5-C8 alkane, a C1-C4 alkanol or a C3-C4 ketone.

### Claim 8 (depends on 7)

The method of claim 7 wherein the solvent comprises water or methanol.

### Claim 9 (depends on 1)

A method for preparing the polymorph Form A of claim 1 comprising,
(A) contacting 8-chloro-6-trifluoromethyl-imidazo[1,2-a]pyridine-2-carbonyl chloride or a salt thereof and 2-chloro-5-methoxybenzene sulfonamide in the presence of a first solvent to form a reaction mixture containing an intermediate solid form of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide,
(B) separating the intermediate solid form of 8-chloro-N-[(2-chloro-5-methoxyphenyl)-sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide, and
(C) contacting the intermediate solid form of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide with a second solvent, optionally heated to a temperature between 30° C. and the boiling point of the second solvent, to convert the intermediate solid form to the polymorph Form A of claim 1.

### Claim 10 (depends on 9)

The method of claim 9 wherein the intermediate solid form of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide is a solvate.

### Claim 11 (depends on 10)

The method of claim 10 wherein the intermediate solid form of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide is a solvate with toluene.

### Claim 12 (depends on 9)

The method of claim 9 wherein the intermediate solid form of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide is an unsolvated polymorph or mixture of polymorphs.

### Claim 13 (depends on 9)

The method of claim 9 wherein the first solvent comprises a mixture of toluene with ethyl acetate and the second solvent comprises water, methanol, acetone or n-heptane.

### Claim 14 (depends on 1)

A nematocidal composition comprising (a) the polymorph Form A of claim 1 and (b) at least one additional component selected from the group consisting of surfactants, solid diluents and liquid carriers.

### Claim 15 (depends on 1)

A nematocidal composition comprising (a) the polymorph Form A of claim 1 and (b) at least one other nematocide, insecticide or fungicide.

### Claim 16 (depends on 1)

A method for protecting a plant from nematodes comprising applying to the plant, or portion, or seed thereof, or to the growing medium of the plant, a nematocidally effective amount of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide comprising the polymorph Form A of claim 1.

### Claim 17 (depends on 15)

The nematicidal composition of claim 15 wherein component (b) is selected from: abamectin, acetamiprid, acrinathrin, amitraz, avermectin, azadirachtin, bifenthrin, buprofezin, carbaryl, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenothiocarb, fenoxycarb, fenvalerate, fipronil, flonicamid, flubendiamide, flufenoxuron, fluvalinate, formetanate, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, lufenuron, metaflumizone, methiodicarb, methomyl, methoprene, methoxyfenozide, nitenpyram, nithiazine, novaluron, oxamyl, pymetrozine, pyrethrin, pyridaben, pyridalyl, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, tebufenozide, tetramethrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, triflumezopyrim, triflumuron, all strains of Bacillus thuringiensis and all strains of Nucleo polyhedrosis viruses.